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Stereochemical studies of some 1,3-disubstituted phthalans

Petracek, F. J. and Sugisaka, Nobuyuki and Klohs, M. W. and Parker, Richard G. and Bordner, Jon and Roberts, John D. (1970) Stereochemical studies of some 1,3-disubstituted phthalans. Tetrahedron Letters, 11 (10). pp. 707-710. ISSN 0040-4039. https://resolver.caltech.edu/CaltechAUTHORS:20151026-093704859

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Abstract

No systematic studies appear to have been reported on the synthesis or methods of assigning the stereochemistry of 1,3-disubstituted phthalans such as 1 - 4. As part of pharmaacological studies (3) on the separated cis-trans isomers of 1-(N,N-dimethylaminomethyl)-3-phenylphthalan (3) prepared sequentially from 1 and 2 it was desirable to establish the stereochemical configurations of the cis-trans isomers of 1-4. We report here nonstereospecific syntheses of 1-4, proton and ^(13)C nmr studies which are somewhat indicative of the configurations, stereoselective syntheses of the cis isomers of 2 - 4 from o-benzoylbenzaldehyde and confirmation of the nmr assignments by X-ray diffraction determination of the crystal structure of trans-1.


Item Type:Article
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http://dx.doi.org/10.1016/S0040-4039(01)97808-6DOIArticle
http://www.sciencedirect.com/science/article/pii/S0040403901978086PublisherArticle
Additional Information:© 1970 Pergamon Press. Received in USA 24 November 1969; received in UK for publication 22 January 1970. The X-ray and 13C nmr studies which were carried on at the California Institute of Technology were supported by the National Science Foundation. Contribution No. 3948.
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Caltech Gates and Crellin Laboratories of Chemistry3848
Issue or Number:10
Record Number:CaltechAUTHORS:20151026-093704859
Persistent URL:https://resolver.caltech.edu/CaltechAUTHORS:20151026-093704859
Official Citation:F.J. Petracek, Nobuyuki Sugisaka, M.W. Klohs, Richard G. Parker, Jon Bordner, John D. Roberts, Stereochemical studies of some 1,3-disubstituted phthalans, Tetrahedron Letters, Volume 11, Issue 10, 1970, Pages 707-710, ISSN 0040-4039, http://dx.doi.org/10.1016/S0040-4039(01)97808-6. (http://www.sciencedirect.com/science/article/pii/S0040403901978086)
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ID Code:61517
Collection:CaltechAUTHORS
Deposited By: Ruth Sustaita
Deposited On:26 Oct 2015 22:06
Last Modified:03 Oct 2019 09:08

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